Dicyclohexylcarbodiimide → HCID 178522679, compound

HRID 614826Notes

Reaction equation

HRID 614826 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:23][C:24]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:25]=1[C:26](O)=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH2:37][C:38]1[NH:42][N:41]=[N:40][N:39]=1>N1C=CC=CC=1>[CH2:16]([O:23][C:24]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:25]=1[C:26]([NH:37][C:38]1[NH:42][N:41]=[N:40][N:39]=1)=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 130269182-(Benzyloxy)-5-(trifluoromethyl)benzoic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178522679HCID 178522679, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N,N'-Dicyclohexylcarbodiimide (1.03 g) was added to a solution of 2-benzyloxy-5-trifluoromethylbenzoic acid (1.48 g) and anhydrous 5-aminotetrazole (0.425 g) in dry pyridine (25 ml), and the resulting mixture was stirred at room temperature for 20 hours. The pyridine was removed in vacuo and the residue was treated with ammonia solution (4N; 75 ml) and stirred for one hour. The insoluble N,N'-dicyclohexylurea was filtered off, and the filtrate was acidified by treatment with concentrated hydrochloric acid. The precipitated solid was recrystallized from ethanol to give 2-benzyloxy-5-trifluoromethyl-N-(tetrazol-5-yl)benzamide (1.25 g), m.p. 248°-249° C. (with decomposition).

Workup

  1. customThe pyridine was removed in vacuo
  2. additionthe residue was treated with ammonia solution (4N; 75 ml)
  3. stirringstirred for one hour
  4. filtrationThe insoluble N,N'-dicyclohexylurea was filtered off
  5. customThe precipitated solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-0805bde26420451faf637632f1989275
Source dataset
uspto-grants-1979_03
Patent number
US04146631

Reaction notes

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